(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

Base Information

Chemical Name:(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one
CAS No.:188786-05-2
Molecular Formula:C₄₆H₈₀O₈Si₂
Molecular Weight:817.307
Hs Code.:

(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

Synonyms:(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

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Chemical Property of (2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

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Technology Process of (2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

There total 7 articles about (2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 123163-78-0
(2S,3R)-3-<(benzyloxy)methoxy>-2-methylpentanal

: 188785-99-1
(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonan-7-one

: 188786-05-2
(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

Guidance literature:: (2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonan-7-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -15 ℃; for 2h;

(2S,3R)-3-<(benzyloxy)methoxy>-2-methylpentanal; In tetrahydrofuran; at -78 ℃; for 1h; Further stages.;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 944740-59-4
(2S,3R,4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonane

: 188786-05-2
(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / BH₃*THF; AlCl₃ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

2.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 1 h / 0 °C

3.1: 85 percent / CaCO₃; Hg(ClO₄)2 / tetrahydrofuran; H₂O / 0.25 h / 20 °C

4.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C

4.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

With aluminium trichloride; mercury(II) perchlorate; borane-THF; N-ethyl-N,N-diisopropylamine; calcium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 944740-67-4
(2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol

: 188786-05-2
(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 18 h / 20 °C

2.1: 96 percent / BH₃*THF; AlCl₃ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

3.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: 85 percent / CaCO₃; Hg(ClO₄)2 / tetrahydrofuran; H₂O / 0.25 h / 20 °C

5.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C

5.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

With aluminium trichloride; mercury(II) perchlorate; borane-THF; N-ethyl-N,N-diisopropylamine; calcium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tet.2007.02.044